5043-03-8Relevant academic research and scientific papers
Rational Design of a Two-Photon Fluorogenic Probe for Visualizing Monoamine Oxidase A Activity in Human Glioma Tissues
Fang, Haixiao,Huang, Wei,Li, Lin,Li, Zheng,Ma, Bo,Ni, Yun,Shi, Riri,Wu, Qiong,Yang, Naidi,Yang, Xuekang,Yao, Shao Q.,Yu, Changmin,Zhang, Chengwu,Zhang, Hang
, p. 7536 - 7541 (2020)
Monoamine oxidases have two functionally distinct but structurally similar isoforms (MAO-A and MAO-B). The ability to differentiate them by using fluorescence detection/imaging technology is of significant biological relevance, but highly challenging with available chemical tools. Herein, we report the first MAO-A-specific two-photon fluorogenic probe (F1), capable of selective imaging of endogenous MAO-A enzymatic activities from a variety of biological samples, including MAO-A-expressing neuronal SY-SY5Y cells, the brain of tumor-bearing mice and human Glioma tissues by using two-photon fluorescence microscopy (TPFM) with minimal cytotoxicity.
Multichromatic fluorescence towards aberrant proteinaceous aggregates utilizing benzimidazole-based ICT fluorophores
An, Jusung,Jangili, Paramesh,Lim, Sungsu,Kim, Yun Kyung,Verwilst, Peter,Kim, Jong Seung
, p. 205 - 215 (2021/07/20)
The pathological origin of Alzheimer’s disease (AD) remains uncharted terrain, despite intensive investigation. Discriminating aberrant proteinaceous deposits, such as β-amyloid (Aβ) and (hyperphosphorylated) tau protein by imaging methods, is a vital tool to support investigations towards the network of interacting features that results in AD pathology. In this context, multispectral fluorescence imaging (MSFI) has drawn much attention enabling the distinction of several analytes with merely a single fluorophore emitting a multichromatic fluorescent signal. Herein, we developed three kinds of benzimidazole-derived fluorescent dyes, BZ1–BZ3. The photophysical properties and intramolecular charge transfer (ICT) characteristics of the probes were evaluated in various solvents. Furthermore, a benzimidazole-associated polar-sensitivity displayed multichromatic behavior and enabled the visualization of minute differences in microenvironmental polarity between Aβ and tau aggregates, resulting in different maximal fluorescent emission wavelengths. Indeed, BZ2 demonstrated an approximately 30?nm bathochromic shift in maximal fluorescent emission. All these observations offer a potential for the development of a future generation of benzimidazole-derived ICT-based fluorescent probes.
ICT-based fluorescent ratiometric probe for monitoring mitochondrial peroxynitrite in living cells
Du, Yuting,Wang, Hongliang,Zhang, Ting,Wei, Wen,Guo, Minmin
supporting information, p. 12915 - 12921 (2021/08/03)
Peroxynitrite (ONOO?) is a reactive oxygen species (ROS) that causes serious damage to living cells and is the cause of a series of human diseases. It is reported that mitochondria are the major site of ONOO?production. Therefore, accurate and rapid detection of intracellular ONOO?is important in pathological processes. Herein, a mitochondria-targeted ratiometric fluorescent probe (DMANI) has been rationally designed based on the coumarin-hemicyanine hybrid framework by regulating the intramolecular charge transfer (ICT) effect. TheDMANIcan capture ONOO?at low concentrationsviadirect addition with the CC bond to give an obvious fluorescent signal change from red to blue based on the ICT process. The possible mechanism for this electrophilic addition process was confirmed using electrospray ionization mass spectrometry (ESI-MS) and1H-NMR spectra.DMANIexhibited a good selectivity, a large Stokes shift (248 nm), a low detection limit (40 nM), and a rapid response (within 20 s) to ONOO?. More importantly,DMANIwas successfully used for ratiometric imaging and monitoring of the fluctuations of mitochondrial ONOO?in living cells.
INHIBITORS OF FIBROBLAST ACTIVATION PROTEIN
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Paragraph 0180, (2020/07/14)
Compounds and compositions for modulating fibroblast activation protein (FAP) are described. The compounds and compositions may find use as therapeutic agents for the treatment of diseases, including hyperproliferative diseases.
A Fluorescent Kinase Inhibitor that Exhibits Diagnostic Changes in Emission upon Binding
Fleming, Cassandra L.,Sandoz, Patrick A.,Inghardt, Tord,?nfelt, Bj?rn,Gr?tli, Morten,Andréasson, Joakim
, p. 15000 - 15004 (2019/09/17)
The development of a fluorescent LCK inhibitor that exhibits favourable solvatochromic properties upon binding the kinase is described. Fluorescent properties were realised through the inclusion of a prodan-derived fluorophore into the pharmacophore of an ATP-competitive kinase inhibitor. Fluorescence titration experiments demonstrate the solvatochromic properties of the inhibitor, in which dramatic increase in emission intensity and hypsochromic shift in emission maxima are clearly observed upon binding LCK. Microscopy experiments in cellular contexts together with flow cytometry show that the fluorescence intensity of the inhibitor correlates with the LCK concentration. Furthermore, multiphoton microscopy experiments demonstrate both the rapid cellular uptake of the inhibitor and that the two-photon cross section of the inhibitor is amenable for excitation at 700 nm.
DANPY (dimethylaminonaphthylpyridinium): an economical and biocompatible fluorophore
Johnson, Lewis E.,Kingsbury, Jason S.,Elder, Delwin L.,Cattolico, Rose Ann,Latimer, Luke N.,Hardin, William,De Meulenaere, Evelien,Deodato, Chloe,Depotter, Griet,Madabushi, Sowmya,Bigelow, Nicholas W.,Smolarski, Brittany A.,Hougen, Trevor K.,Kaminsky, Werner,Clays, Koen,Robinson, Bruce H.
supporting information, p. 3765 - 3780 (2019/04/16)
Dyes with nonlinear optical (NLO) properties enable new imaging techniques and photonic systems. We have developed a dye (DANPY-1) for photonics applications in biological substrates such as nucleic acids; however, the design specification also enables it to be used for visualizing biomolecules. It is a prototype dye demonstrating a water-soluble, NLO-active fluorophore with high photostability, a large Stokes shift, and a favorable toxicity profile. A practical and scalable synthetic route to DANPY salts has been optimized featuring: (1) convergent Pd-catalyzed Suzuki coupling with pyridine 4-boronic acid, (2) site-selective pyridyl N-methylation, and (3) direct recovery of crystalline intermediates without chromatography. We characterize the optical properties, biocompatibility, and biological staining behavior of DANPY-1. In addition to stability and solubility across a range of polar media, the DANPY-1 chromophore shows a first hyperpolarizability similar to common NLO dyes such as Disperse Red 1 and DAST, a large two-photon absorption cross section for its size, substantial affinity to nucleic acids in vitro, an ability to stain a variety of cellular components, and strong sensitivity of its fluorescence properties to its dielectric environment.
White-light emission from a structurally simple hydrazone
Shao, Baihao,Stankewitz, Nell,Morris, Jacob A.,Liptak, Matthew D.,Aprahamian, Ivan
supporting information, p. 9551 - 9554 (2019/08/15)
Two hydrazones featuring a unique excitation wavelength-dependent dual fluorescence emission have been developed. The mixing extent of the two emission bands can be modulated by tuning the excitation wavelength, resulting in multicolor and even white light emission from structurally simple hydrazones.
A mitochondria-targeted two-photon fluorogenic probe for the dual-imaging of viscosity and H2O2 levels in Parkinson's disease models
Li, Hao,Xin, Chenqi,Zhang, Gaobin,Han, Xisi,Qin, Wenjing,Zhang, Cheng-Wu,Yu, Changmin,Jing, Su,Li, Lin,Huang, Wei
supporting information, p. 4243 - 4251 (2019/07/16)
Parkinson's disease (PD) is a neurodegenerative disease that seriously affects the quality of life of the patient. Many sources have shown that mitochondrial dysfunction is increasingly appreciated as playing a critical role in the pathogenesis of PD. The mitochondrial microenvironment and H2O2 level are two key parameters that are used to assess the function of mitochondria. Herein, we designed and synthesized a novel two-photon (TP) fluorogenic probe Mito-LX, which could simultaneously monitor changes in the mitochondrial viscosity and H2O2 levels using two different channels. This probe showed a significant response to viscosity changes with red emission at 730 nm and high sensitivity to H2O2 levels with orange emission at 585 nm. Moreover, Mito-LX was successfully applied to living systems (including living cells, zebrafish and Drosophila) for viscosity and H2O2 detection using one- and two-photon fluorescence confocal microscopy.
Specific two-photon fluorescent probe of monoamine oxidase A, and preparation method and application thereof
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Paragraph 0035; 0037-0039, (2019/10/29)
The invention relates to a specific two-photon fluorescent probe of monoamine oxidase A, and a preparation method and an application thereof, belonging to the field of organic fluorescent probes. Thespecific two-photon fluorescent probe comprises a compound F1 with a general formula (I) which is described in the specification; and the probe is designed by utilizing the spatial selectivity of enzyme and combining the idea of constructing a conjugated structure. The probe F1 successfully and specifically detects the activity of MAO-A in different biological samples (pure proteins, cell lysates,viable cells, mouse brain tissues and tumor tissues). The probe has high sensitivity and low cost, and is applicable to industrialization.
Histone deacetylase fluorescence probe, and preparation method and applications thereof
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Paragraph 0040, (2018/07/30)
The invention provides a histone deacetylase fluorescence probe, and a preparation method and applications thereof. The structure formula of the histone deacetylase fluorescence probe is disclosed inthe invention. In synthesis, 6-(dimethylamino)-2-naphthaldehyde with two-photon effect is selected as a dye, so that further nucleophilic reaction is realized after deacetylation reaction, and fluorescence signals are generated; aldehyde group carbon is modified into cyanogroup alcohol structures, hydroxyl is connected with HDACs responsive groups, and the histone deacetylase fluorescence probe isused for detecting and imaging of the activity of histone deacetylase in tissue. According to the histone deacetylase fluorescence probe, cyanogroup with excellent electron-withdrawing capability isintroduced, so that after response of HDACs with the histone deacetylase fluorescence probe, intramolecular cyclization reaction is carried out rapidly, activation of fluorescence signals is realized,detecting and imaging on histone deacetylase in living cells and tissue are realized, and excellent clinical application value is achieved.
